An unprecedented antioxidative isopimarane norditerpenoid from bivalve clam, Paphia malabarica with anti-cyclooxygenase and lipoxygenase potential

References

• Ajay Walters WP, Murcko MA. 1998. Can we learn to distinguish between “drug-like” and “nondrug-like” molecules? J Med Chem. 41:3314–3324.
   PubMed Web of Science ®Google Scholar
• Baylac S, Racine P. 2003. Inhibition of 5-lipoxygenase by essential oils and other natural fragment extracts. Int J Aromather. 13:138–142.
   Web of Science ®Google Scholar
• Benkendorff K. 2010. Molluscan biological and chemical diversity: secondary metabolites and medicinal resources produced by marine molluscs. Biol Rev Camb Philos Soc. 85:757–775.
   PubMed Web of Science ®Google Scholar
• Bian W-T, You Z-J, Wang C-Y, Shao C-L. 2014. Brominated pimarane diterpenoids from the sea hare Aplysia pulmonica from the South China Sea. Chem Nat Comp. 50:557–559.
   Web of Science ®Google Scholar
• Botting RM. 2006. Inhibitors of cyclooxygenases: mechanisms, selectivity and uses. J Physiol Pharmacol. 57:113–124.
   PubMed Web of Science ®Google Scholar
• Bromann K, Viljanen K, Moreira VM, Yli-Kauhaluom J. 2014. Isolation and purification of ent-pimara-8(14), 15-diene from engineered Aspergillus nidulans by accelerated solvent extraction combined with HPLC. Anal Methods. 6:1227–1234.
   Web of Science ®Google Scholar
• Chakraborty K, Chakkalakal SJ, Joseph D, Asokan PK, Vijayan KK. 2016. Nutritional and antioxidative attributes of green mussel (Perna viridis L.) from the southwestern coast of India. J Aquat Food Prod Technol. 25:968–985.
   Web of Science ®Google Scholar
• Chakraborty K, Chakkalakal SJ, Joseph D. 2014. Response of pro-inflammatory prostaglandin contents in anti-inflammatory supplements from green mussel Perna viridis L. in a time-dependent accelerated shelf-life study. J Funct Food. 7:527–540.
   Web of Science ®Google Scholar
• Chew YL, Lim YY, Omar M, Khoo KS. 2008. Antioxidant activity of three edible seaweeds from two areas in South East Asia. LWT-Food Sci Technol. 41:1067–1072.
   Web of Science ®Google Scholar
• Costantino V, Fattorusso E, Mangoni A, Perinu C, Cirino G, De Gruttola L, Roviezzo F. 2009. Tedanol: a potent anti-inflammatory ent-pimarane diterpene from the Caribbean Sponge Tedania ignis. Bioorg Med Chem. 17:7542–7547.
   PubMed Web of Science ®Google Scholar
• D’Orazio N, Gammone AM, Gemello E, De Girolamo M, Cusenza S, Riccioni G. 2012. Marine bioactives: pharmacological properties and potential applications against inflammatory diseases. Mar Drugs. 10:812–833.
   PubMed Web of Science ®Google Scholar
• Oh D-C, Jensen PR, Kauffman CA, Fenical W. 2005. Libertellenones A–D: induction of cytotoxic diterpenoid biosynthesis by marine microbial competition. Bioorg Med Chem. 13:5267–5273.
   PubMed Web of Science ®Google Scholar
• Gonzalez PM, Malanga G, Puntarulo S. 2015. Cellular oxidant antioxidant network: update on the environmental effects over marine organisms. Open Mar Biol J. 9:1–13.
   Google Scholar
• Huang SZ, Ma QY, Fang WW, Xu FQ, Peng H, Dai HF, Zhou J, Zhao YX. 2013. Three new isopimarane diterpenoids from Excoecaria acerifolia. J Asian Nat Prod Res. 15:750–755.
   PubMed Web of Science ®Google Scholar
• Joy M, Chakraborty K, Pananghat V. 2016. Comparative bioactive properties of bivalve clams against different disease molecular targets. J Food Biochem. 40:593–602.
   Web of Science ®Google Scholar
• Joy M, Chakraborty K. 2016. Nutritional qualities of the low value bivalve mollusks Paphia malabarica and Villorita cyprinoids at the estuarine waters of southwestern coast of India. J Aquat Food Prod T. Online publication date 2016/2/1 (in press). doi: 10.1080/10498850.2015.1092486.
   Web of Science ®Google Scholar
• Laneuville O, Breuer DK, DeWitt DL, Hla T, Funck CD, Smith WL. 1994. Differential inhibition of human prostaglandin endoperoxide H synthases-1 and -2 by nonsteroidal anti-inflammatory drugs. J Pharmacol Exp Ther. 271:927–934.
   PubMed Web of Science ®Google Scholar
• Larsen LN, Dahl E, Bremer J. 1996. Peroxidative oxidation of leuco-dichloroluorescein by prostaglandin-H synthase in prostaglandin biosynthesis from polyunsaturated fatty acids. Biochim Biophys Acta. 1299:47–53.
   PubMed Web of Science ®Google Scholar
• Lushchak V. 2011. Environmentally induced oxidative stress in aquatic animals. Aquat Toxicol. 101:13–30.
   PubMed Web of Science ®Google Scholar
• Ma GX, Yin L, Wang TS, Pan Y, Guo LW. 1998. A 19-carbon pimarane-type diterpenoid from Ephemerantha fimbriata. Pharm Biol. 36:66–68.
   Web of Science ®Google Scholar
• Mitchell JA, Akarasereenont P, Thiemermann C, Flower RJ, Vane JR. 1994. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc Natl Acad Sci USA. 90:11693–11697.
   Web of Science ®Google Scholar
• Nagash YS, Nazeer RA, Kumar NSS. 2010. In vitro antioxidant activity of solvent extracts of mollusks (Loligo duvauceli and Donax strateus) from India. World J Fish Mar Sci. 2:240–245.
   Google Scholar
• Porto TS, Rangel R, Furtado NAJC, de Carvalho TC, Martins CG, Veneziani RCS, Da Costa FB, Vinholis AHC, Cunha WR, Heleno VCG, et al. 2009. Pimarane-type diterpenes: antimicrobial activity against oral pathogens. Molecules. 14:191–199.
   PubMed Web of Science ®Google Scholar
• Quan L-D, Thiele GM, Tian J, Wang D. 2008. The development of novel therapies for rheumatoid arthritis. Expert Opin Ther Pat. 18:723–738.
   PubMed Web of Science ®Google Scholar
• Schmitz FJ, Michaud DP, Schmidt PC. 1982. Marine natural products: Parguerol, deoxyparguerol, and isoparguerol. New brominated diterpenes with modified pimarane skeletons from the sea hare Aplysia dactylomela. J Am Chem Soc. 104:6415–6423.
   Web of Science ®Google Scholar
• Schnitzer J, Kamin M, Olson WH. 1999. Tramadol allows reduction of naproxen dose among patients with naproxen-responsive osteoarthritis pain. Arthritis Rheum. 42:1370–1377.
   PubMed Web of Science ®Google Scholar
• Sprangler RS. 1996. COX-2 activity can reduce the level of toxicity for a given NSAID but may not be sufficient to overcome toxicities resulting from other mechanisms. Semin Arthritis Rheum. 26:436–447.
   Google Scholar
• Sun L, Li D, Tao M, Chen Y, Dan F, Zhang W. 2012. Scopararanes C-G: new oxygenated pimarane diterpenes from the marine sediment-derived fungus Eutypella scoparia FS26. Mar Drugs. 10:539–550.
   PubMed Web of Science ®Google Scholar
• Takeda S, Kurosawa E, Komiyama K, Suzuki T. 1990. The structures of cytotoxic diterpenes containing bromine from the marine red alga Laurencia obtusa (Hudson) Lamouroux. Bull Chem Soc Jpn. 63:3066–3072.
   Web of Science ®Google Scholar
• Vijayabaskar P, Shiyamala V. 2012. Antioxidant properties of seaweed polyphenol from Turbinaria ornata (Turner) J. Agardh, 1848. Asian Pac J Trop Biomed. 2:S90–S98.
   Google Scholar
• Wang F, Cheng XL, Li Y-J, Shi S, Liu J-K. 2009. ent-Pimarane diterpenoids from Siegesbeckia orientalis and structure revision of a related compound. J Nat Prod. 72:2005–2008.
   PubMed Web of Science ®Google Scholar
• Wang XN, Bashyal BP, Wijeratne EMK, U’Ren JM, Liu MX, Gunatilaka MK, Arnold AE, Gunatilaka AAL. 2011. Smardaesidins A-G, isopimarane and 20-nor-isopimarane diterpenoids from Smardaea sp., a fungal endophyte of the moss Ceratodon purpureus. J Nat Prod. 74:2052–2061.
   PubMed Web of Science ®Google Scholar
• Whitehouse MW, Macrides TA, Kalafatis N, Betts WH, Haynes DR, Broadbent J. 1997. Anti-inflammatory activity of a lipid fraction (lyprinol) from the NZ green-lipped mussel . Inflammopharmacology. 5:237–246.
   PubMedGoogle Scholar
• Xia X, Qi J, Liu Y, Jia A, Zhang Y, Liu C, Gao C, She Z. 2015. Bioactive isopimarane diterpenes from the fungus, Epicoccum sp. HS-1, associated with Apostichopus japonicus. Mar Drugs. 13:1124–1132.
   PubMed Web of Science ®Google Scholar